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January 6, 2022

Anytime is a Great Time in Anguilla

If you plan to charter a yacht and cruise the Leeward Islands, then Anguilla should definitely be on the itinerary. This long thin thirty-five square mile British overseas territory is aptly named after the French word for eel, anguille. It is the most northerly of the Leeward chain and is just twelve miles north of Saint Martin, St Maarten. It is sixty miles northwest of St. Kitts so it is easily reachable from most of the entire Leeward archipelago.

Turquoise sea and white sandy beach of Anguilla

Anguilla is a laid-back paradise with white sandy beaches, sparkling azure waters, and welcoming friendly people. It is made up of the main island and several uninhabited offshore islands including Dog, Scrub, Sombrero, and the Prickly Pear Cays. The tropical climate is amazing year-round as the constant trade winds bring in a comforting breeze.

High season is also the driest time of year from December through April, but the remainder of the year has its advantages as well. If you plan to come in the summer during hurricane season, you may get lower rates and the opportunity to enjoy one of the most festive times on Anguilla. Usually occurring in late July or early August, Carnival is a lively celebration with pageants, musical performances, and the Parade of Troupes, where colorfully costumed dancers perform in the streets. It showcases the artistry, hospitality, and innovation of the Anguillan people.

Beaches of Anguilla

Fittingly, because it is a small island surrounded by big waters with an exciting nautical history, boat racing is the national sport of Anguilla. The sport came about during a time when Anguillans were looking for ways to earn a living, so they sailed to the Dominican Republic to work in the sugar cane fields. After months of hard labor, the workers were eager to return home to Anguilla. Their desperate return became a race between captains to get home first,  while families lined the hills and shores for a glimpse of their family members returning. When the boats were in sight, they would all run to Sandy Ground to welcome the working men home. The boats that brought the sugar cane workers home have evolved into the racing boats of today.

Anguilla boat racing is unique and the sailboats are not typical sailing vessels. They are highly decorated, deep keeled, have oversized sails, with no decks, and are now built chiefly for racing. The competitors are passionate and prepare all year for boat racing season. Likewise, the fans are very invested in the sport, animatedly debating about the performance of their favorite boats. Most of the island’s villages have their own boats and large dedicated crews that daringly navigate the rocky waters surrounding the island.

Traditional wood racing boat crew on the Caribbean island of Anguilla

If you plan to charter in the spring and summer, you might encounter one of the many sail racing events. If you are there during Carnival, you will encounter the most popular and festive race known as August Monday. People from all over the Caribbean come to Anguilla for this important event, and the beach along Sandy Ground is packed with partygoers, spectators, and racers as they barbecue, dance to calypso music, and indulge in tropical drinks all day until the race begins in the late afternoon. As the boats depart to race around the island, spectators grab binoculars and jump into pick-up trucks driving to vantage points around the island to cheer on their favorites. Additionally, the racers are accompanied on the water by party boats and private boats wanting to join in on the festive spirit that makes this race so exciting and beloved.

The races are quite riveting as Anguilla sailboat racing does not follow the international sailing regulations regarding right of way. In Anguilla, boats will shout, “Hard Lee” when they are on a collision course, after which the boats must tack. At times, crews who are reluctant to change course do not tack and the racing vessels miss each other by mere inches. Also unique to Anguilla boat racing is that crew members are sometimes used as ballasts and when the boat is too heavy to maneuver, crew members are sometimes tossed overboard in order to gain a competitive advantage. If you are unable to make it to the “Super Bowl” of Anguilla boat racing during Carnival, other notable events include the Easter Monday race, Anguilla Day at the end of May, Queen’s Day in June, August Thursday during the first Thursday in August and Champion of Champions which takes place the following Sunday.

Beautiful beach framed with palms and seaside cafe on the Caribbean island of Anguilla

A stop-over in Anguilla during the spring or summer might allow you to join in on some of these culturally rich events. However, if you are unable to get there to enjoy Anguilla boat racing season, the easygoing atmosphere, glistening beaches, brilliant blue waters, remote scenic bays, and perfect tropical climate make Anguilla amazing any time of year.

For more information on booking a charter in Anguilla, please leave us your details and we will reach out to you shortly.